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Vacation rentals with outdoor seating in Chilmark

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Chilmark

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

The exterior of the renovated barn showcases a charming cottage-style design with gray shingle siding. A well-maintained lawn is surrounded by a variety of colorful flowers and shrubs, enhancing the natural setting. Large windows allow for ample natural light while adding character to the home.

Home in Chilmark

4.99 out of 5 average rating, 101 reviews

Renovated Barn in Chilmark 3BR

This renovated barn is a well maintained ranch/cottage style home that is located just off of North Road, minutes from Menemsha. An open living dining/kitchen area make for a welcoming area. It has a breakfast bar, vaulted ceilings, flat screen TV, lovely back deck, outdoor shower, 2 full bathrooms and 3 spacious bedrooms. The house is located just across the street from Menemsha Hills conservation area, providing hiking trails and access to North Shore beach. Lucy Vincent and Squibnocket Beach stickers are also available. Help with boat tickets available.

The main sleeping area features a spacious wooden bed with grey linens and two light blue towels neatly arranged on the bed. Two bedside tables with lamps flank the bed, and large windows with black shades provide a view of the greenery outside.

Guest suite in West Tisbury

4.92 out of 5 average rating, 144 reviews

Studio Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this airy suite has vaulted wood ceilings with skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is prime and centrally located, just off historic Music St, a short walk to our small town center which provides many amenities. Ask about our other private guest suite if you are traveling with others

A vibrant green kayak glides over calm waters, with a person seated inside holding a paddle. In the background, a cottage displays large wall-to-wall windows reflecting the surrounding trees, providing a connection to nature.

Cottage in Sandwich

4.95 out of 5 average rating, 239 reviews

WOW LAKE VIEW! Waterfront, Prvt Beach, King Bed!

Wake up to magnificent panoramic views of a beautiful lake with waves lapping below your window! See a video tour on YouTube: "WOW View! Cape Cod Lakefront Cottage. Private Beach, King bed" Guests love the stylish, peaceful, open design; wall-to-wall, floor-to-ceiling windows; private beach with picnic table and chaise lounge chairs; a full, modern kitchen; luxurious King gel/coil bed, private office, bathroom's curved shower, AC, and much more! It's like being on your own luxury houseboat!

A charming post and beam house is set back from a sandy driveway, surrounded by lush greenery and colorful flowers. Large windows on the upper level allow for natural light, providing a welcoming entrance to the home.

Home in West Tisbury

4.97 out of 5 average rating, 150 reviews

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

Top guest favorite

An open studio space features a cozy sleeping area with a spacious bed covered in light bedding. A soft armchair and a wooden bench provide additional seating. Natural light streams in from a window, enhancing the room's bright atmosphere. Shelving displays books and decorative items.

Apartment in Oak Bluffs

4.98 out of 5 average rating, 219 reviews

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

The exterior of a newly constructed guest house is shown, featuring a spacious deck with seating arrangements. Surrounding plant beds with fresh landscaping complement the wooden structure, while a gravel pathway leads towards the entrance, creating an inviting outdoor space.

Home in Edgartown

4.96 out of 5 average rating, 247 reviews

Brand new gorgeous 2 bedroom guest house.

This is a gorgeous brand new 2 bedroom guest house on the bike path that leads to downtown Edgartown and both State Beach and South Beach, as well as 1/4 of a mile from the famous Morning Glory Farm Stand. There are cathedral ceilings in the living room, which provide a open, spacious feel. There is a large deck on the front of the house with a grill, table and chairs. Part of it is covered in shade. Separate parking for guests with privacy, as it sits 200+ feet from the main house.

Top guest favorite

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guesthouse in Chilmark

4.99 out of 5 average rating, 102 reviews

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

Top guest favorite

A cozy outdoor seating area is arranged with several white lounge chairs on a gravel surface. A brick fireplace is positioned near the house, accompanied by potted plants and a view of the deck area adorned with covered furniture in the background.

Cottage in Tisbury

4.98 out of 5 average rating, 344 reviews

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

The exterior of the yurt showcases a circular wooden structure with large, rounded windows, complemented by a metal roof. A private yard features lush greenery, colorful flora, and outdoor seating arrangements, creating an inviting space for relaxation and outdoor activities.

Home in Oak Bluffs

4.92 out of 5 average rating, 273 reviews

Unique Luxury Yurt w/ Free kayaking

Step into this unique yurt house! As soon as you walk in, you'll be greeted with a one-of-a-kind experience, from the textured concrete floors to the large circular skylight. Every detail is carefully planned, and you'll have the opportunity to unwind in a spacious private yard. Spend your evenings stargazing, take advantage of complimentary paddling, participate in our scheduled chicken feedings, do yoga in the roomy loft, and revel in the splendor of your exclusive island yurt!

The front exterior of the house is shown surrounded by lush greenery, featuring a well-maintained lawn. A pathway leads to the entrance, and the porch offers seating. Two sun loungers are positioned on the grass, inviting relaxation in the open space.

Home in Oak Bluffs

4.91 out of 5 average rating, 127 reviews

** Vineyard Vacation Retreat ** with HOT TUB

Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell driveway. The house is filled with art from local artist Alan Whiting, Colin Rule, Kara Taylor and Scott McDowell. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home. Updated 7/25/2025 we do not have any more firewood on the property.

A modern kitchen features a spacious island with two black bar stools. Stainless steel appliances, including a microwave and toaster, complement quartz countertops. Natural light fills the space through large windows, revealing a glimpse of greenery outside.

Cottage in Oak Bluffs

4.96 out of 5 average rating, 151 reviews

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

Top guest favorite

A cozy living area features a comfortable gray sofa with decorative pillows and a wooden coffee table. Natural light fills the space, highlighting a dining table with four chairs. A doorway leads to the kitchen, while a wall-mounted TV provides entertainment options.

Guest suite in West Falmouth

4.99 out of 5 average rating, 177 reviews

The Sea-Cret Garden, Guest Apartment

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

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Popular amenities for Chilmark outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

A spacious bed is centered against a light grey wall, featuring a wooden headboard. Colorful coral-patterned pillows add a subtle touch. Two bedside tables with lamps sit on either side, creating a balanced and calming atmosphere.

Home in Mattapoisett

4.94 out of 5 average rating, 218 reviews

*The Cozy Escape* | Historic South Coast Retreat

A gravel driveway leads to a charming house with a red garage. A wooden pergola, adorned with greenery, provides shade along the entrance. Lush trees and open sky enhance the serene outdoor setting, inviting visitors to explore the surrounding landscape.

Home in West Tisbury

4.96 out of 5 average rating, 50 reviews

Vineyard Meadow Writer's Cottage

Top guest favorite

The exterior of the charming cottage is surrounded by lush greenery and mature trees. A well-maintained path leads to the entrance, framed by a green hedge. The inviting façade features a sloping roof and bright windows, creating a serene rural atmosphere.

Home in Woods Hole

4.93 out of 5 average rating, 123 reviews

Juniper Point Cottage With Ocean View

A sunlit sunroom features wooden beams overhead, creating an airy atmosphere. Comfortable seating includes a neutral sectional sofa and various ottomans. Vibrant cushions add color, and large glass windows offer views of the outdoor patio area, enhancing the connection to nature.

Home in West Tisbury

4.83 out of 5 average rating, 46 reviews

Charming and Spacious Home in the Heart of MV

The rustic farmhouse is framed by lush greenery and colorful flowers in the foreground. A well-maintained lawn leads to the side of the house, which is partially obscured by trees. The home features a charming wooden exterior, blending harmoniously with its natural surroundings.

Home in West Tisbury

4.88 out of 5 average rating, 34 reviews

Greenehill~ Up-island 1800's Vineyard farmhouse.

A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.

Home in Tisbury

4.93 out of 5 average rating, 146 reviews

Vineyard Haven Walk to Ferry

Top guest favorite

A spacious, newly constructed home is showcased with a dark blue exterior and white accents. The façade features a prominent front porch with chairs and a large garage. A gravel driveway leads to the entrance, framed by a lush green lawn and trees.

Home in Oak Bluffs

4.97 out of 5 average rating, 37 reviews

The Blue Lagoon, Oak Bluffs

Top guest favorite

A cozy living area features a stone fireplace, with a muted flame providing a warm glow. Above, a flat-screen TV is mounted against white shiplap walls, complemented by exposed beams. A dark wood coffee table sits at the center, surrounded by comfortable seating and decorative accents.

Home in New Bedford

4.99 out of 5 average rating, 251 reviews

Historic Cobblestone Carriage House near Downtown

Apartment rentals with outdoor seating

A charming waterfront building with a distinct blue facade features multiple balconies lined with railing. A lively outdoor dining area is visible on the lower level. Surrounding structures reflect a lively coastal atmosphere, with clear skies and people enjoying the vibrant setting.

Apartment in Oak Bluffs

4.88 out of 5 average rating, 163 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

Top guest favorite

A spacious garden area is shown, featuring a large tree providing shade alongside the main residence. Lush green grass extends throughout the yard, complemented by colorful flower beds. A stone border outlines the garden, enhancing the serene outdoor environment.

Apartment in Westport

4.94 out of 5 average rating, 280 reviews

15 Acres of Open Fields & 15 Minutes to the Beach

Top guest favorite

Apartment in New Bedford

4.91 out of 5 average rating, 320 reviews

Walk downtown from our terrace apartment

A cozy living area is presented with a dark couch and a wooden dining table accompanied by black chairs. A TV is situated on a light-colored media unit, while bookshelves filled with books line one wall. Natural light filters in through sheer curtains.

Apartment in Fairhaven

4.78 out of 5 average rating, 117 reviews

Main Street on the Park

The inviting front of a blue house features a warm entry door flanked by two outdoor light fixtures. A stone pathway leads to the door, bordered by vibrant flowerbeds filled with sunflowers, daisies, and other colorful blooms, enhancing the home's welcoming appearance.

Apartment in Barnstable

4.95 out of 5 average rating, 125 reviews

Centerville Studio with Town Beach Pass

A small outdoor balcony features a sleek table set for two, adorned with vibrant blue cushions on barstools. In the background, the view reveals a shimmering bay dotted with boats and framed by trees, showcasing the serene waterfront environment.

Apartment in Wareham

4.93 out of 5 average rating, 169 reviews

⭐ Gorgeous Beach Views -- The Sand Dollar Suite

Top guest favorite

Two black Adirondack chairs are positioned around a small table in a serene backyard setting. A bowl filled with lobster sits atop the table, with a fish pond and rocks in the background, complemented by sun rays filtering through the foliage.

Apartment in Sandwich

5 out of 5 average rating, 103 reviews

Cozy Large Private Pet Friendly Studio

Top guest favorite

Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.

Apartment in Little Compton

4.96 out of 5 average rating, 339 reviews

Home by the Sea

Condo rentals with outdoor seating

A two-story home is set amid lush greenery, featuring a well-manicured lawn and a large tree offering shade. The exterior displays classic architectural elements, with white siding and black shutters. A sign marked '1846' is visible beside the pathway, inviting exploration.

Condo in Falmouth

4.89 out of 5 average rating, 28 reviews

Heart of downtown, walk to ferry, bikeway & beach!

An open lounge area features a comfortable seating arrangement, including a white sofa and patterned armchair. A wooden coffee table sits at the center, complemented by a glass side table. The room is illuminated by track lighting, with windows providing natural light and views.

Condo in New Bedford

4.71 out of 5 average rating, 42 reviews

Crow's Nest Down Town New Bedford.

A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.

Condo in Tisbury

4.92 out of 5 average rating, 49 reviews

Private 3bdrm Condo Tashmoo Woods

A cozy living and dining area features a light-colored sofa with decorative throw pillows, complemented by a wooden dining table surrounded by four chairs. A fireplace, framed art, and a warm-toned lamp enhance the space, while a patterned rug adds a touch of comfort.

Condo in Oak Bluffs

4.67 out of 5 average rating, 3 reviews

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

An aerial view captures the resort's layout alongside the coastline. Sandy beach stretches along the water's edge, while the Atlantic Ocean meets a calm bay. Behind the resort, residential areas are interspersed with patches of greenery, illustrating the natural beauty surrounding the location.

Condo in East Falmouth

4.63 out of 5 average rating, 8 reviews

InnSeason Resorts Surfside

A two-story house is set on a lush green lawn, framed by vibrant flowering bushes. Stone steps lead up to a white front door, flanked by large windows. A partial second-floor deck is visible above the entrance, with a clear blue sky overhead.

Condo in Tisbury

4.91 out of 5 average rating, 81 reviews

Sunny 2bedroom condo w pool, walk to town

Top guest favorite

A private deck features a glass-topped table set for dining, surrounded by black metal chairs. Soft blue cushions add comfort to the seating area, while a vase with yellow tulips brings a pop of color. The tranquil view of Deans Pond complements the inviting outdoor space.

Condo in New Seabury

4.95 out of 5 average rating, 82 reviews

Beach Cottage 3nts/4th Free Aug - Oct Mashpee MA

A light-filled living room features a comfortable gray sofa, a white coffee table, and a cozy armchair beside a decorative fireplace. Blue walls are complemented by plush rugs and curtains, while a flat-screen TV is mounted above the fireplace, creating an inviting space.

Condo in Hyannis Port

4.85 out of 5 average rating, 92 reviews

Short walk to the Beach and Downtown Hyannis!

Quick stats about vacation rentals with outdoor seating in Chilmark

Total rentals
130 properties
Nightly prices starting at
R3,126 ZAR before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace

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